Sulfuric Acid → HCID 12810993, compound

HRID 1105769Notes

Reaction equation

HRID 1105769 reaction equation
[OH:1][C:2]1[C:7]([C:8](OC)=O)=[C:6]([CH3:12])[CH:5]=[C:4]([CH2:13][CH2:14][C:15]([OH:33])([CH3:32])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:31])[CH2:20][CH2:21][CH2:22][CH:23]([CH3:30])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:3]=1[C:34](OC)=O.S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1.C1C=CC=CC=1>[CH3:8][C:7]1[C:6]([CH3:12])=[CH:5][C:4]([CH2:13][CH2:14][C:15]([OH:33])([CH3:32])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:31])[CH2:20][CH2:21][CH2:22][CH:23]([CH3:30])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:28])[CH3:29])=[C:3]([CH3:34])[C:2]=1[OH:1]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 12810992HCID 12810992, compound

Product 1

HCID 12810993HCID 12810993, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 7237O-XyleneSolvent

Procedure

To a solution of the dimethyl 2-hydroxy-4-methyl-6-(3-hydroxy-3,7,11,15-tetramethyl-hexadecanyl)-benzene-1,3-dicarboxylate (5.17 g) in xylene (25 ml) at 10° was added sodium dihydrobis(2-methoxyethoxy)aluminate (20 ml of a 70% by weight solution in benzene) over 20 min with occasional cooling to keep the temperature at 10°. After 10 min the solution was heated to reflux for 1.5 hr, cooled to 10° and was poured cautiously into cold 20% by weight aqueous sulfuric acid (200 ml). The mixture was extracted with ether (3×100 ml) and the combined extracts were washed with aqueous sodium bicarbonate and brine and dried (Na2SO4) and concentrated on a rotary evaporator to give 4.29 g of crude 2,3,6-trimethyl-5-(3-hydroxy-3,7,11,15-tetramethylhexadecanyl)-phenol as a light yellow oil. Chromatography on silica gel eluting with ether in petroleum ether gave 3.19 g of pure 2,3,6-trimethyl-5-(3-hydroxy-3,7,11,15-tetramethylhexadecanyl)-phenol.

Workup

  1. temperaturewith occasional cooling
  2. customat 10°
  3. temperatureAfter 10 min the solution was heated
  4. temperatureto reflux for 1.5 hr
  5. temperaturecooled to 10°
  6. extractionThe mixture was extracted with ether (3×100 ml)
  7. washthe combined extracts were washed with aqueous sodium bicarbonate and brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-beab980b8ef748d281182cf06d49a2f9
Source dataset
uspto-grants-1982_01
Patent number
US04310465

Reaction notes

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