Hydrochloric Acid → 4-{3-[3,4-Bis(hydroxymethyl)phenyl]propyl}-2-ethylphenol

HRID 970842Notes

Reaction equation

HRID 970842 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[C:15]([C:23](OC)=[O:24])[C:16](=[CH:21][CH:22]=2)[C:17](OC)=[O:18])[CH:6]=[CH:7][C:8]=1[OH:9])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].Cl>C(OCC)C.O>[OH:24][CH2:23][C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][CH2:10][C:5]2[CH:6]=[CH:7][C:8]([OH:9])=[C:3]([CH2:1][CH3:2])[CH:4]=2)[CH:22]=[CH:21][C:16]=1[CH2:17][OH:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 17983037Dimethyl 4-[3-(3-ethyl-4-hydroxyphenyl)propyl]phthalateHCID 21226445Aluminium lithium hydride

Product 1

HCID 694919444-{3-[3,4-Bis(hydroxymethyl)phenyl]propyl}-2-ethylphenol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

1.7 g (4.8 mmol) of dimethyl 4-[3-(3-ethyl-4-hydroxyphenyl)propyl]phthalate (Example 1f are dissolved in 50 ml of ethyl ether, and this solution is slowly added to a suspension of 435 mg (11.4 mmol) of lithium aluminum hydride. The medium is stirred for 30 minutes and is then sequentially treated with 450 μl of water, 450 μl of 15% sodium hydroxide and 1.5 ml of water. The reaction medium is poured into a 1N hydrochloric acid solution, and extracted with ethyl ether. A white solid is obtained (m=1.2 g, m.p.=82° C., y=84%).

Workup

  1. extractionextracted with ethyl ether
  2. customA white solid is obtained (m=1.2 g, m.p.=82° C., y=84%)

Sources & evidence

ORD record
ord-4cbc5384fc2742e79d5cd97654289acc
Source dataset
uspto-grants-2007_12
Patent number
US07312249B2

Reaction notes

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