Sulfuric Acid → 4-(1-Hydroxy-2,6,6-trimethyl-cyclohex-3-en-1-yl)-but-3-yn-2-ol

HRID 2285669Notes

Reaction equation

HRID 2285669 reaction equation
CC([O:6][CH:7]([C:9]#[CH:10])[CH3:8])OCC.C([Mg]Br)C.[CH3:15][CH:16]1[CH:21]=[CH:20][CH2:19][C:18]([CH3:23])([CH3:22])[C:17]1=[O:24].OS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)C>[OH:24][C:17]1([C:10]#[C:9][CH:7]([OH:6])[CH3:8])[C:18]([CH3:23])([CH3:22])[CH2:19][CH:20]=[CH:21][CH:16]1[CH3:15]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 100120033-(1-Ethoxyethoxy)but-1-yneHCID 197996892,6,6-Trimethyl-cyclohex-3-en-1-oneHCID 178418443HCID 178418443, compound

Product 1

HCID 204580054-(1-Hydroxy-2,6,6-trimethyl-cyclohex-3-en-1-yl)-but-3-yn-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5.5 g of 2-(3-oxa-pent-2-yloxy)-but-3-yne (see Example 2, letter a), 14 ml of 40% ethyl-magnesium bromide in diethyl ether and 3.5 g of 2,6,6-trimethyl-cyclohex-3-en-1-one in anhydrous diethyl ether were reacted as described in Example 2 (letter b). The crude reaction mixture was then acidified with 35% aqueous H2SO4 and stirred during 2 hours at 20°. After addition of 10% aqueous Na2CO3 until neutrality, extraction with diethyl ether, drying of the organic phase over Na2SO4 and evaporation, there were isolated 0.4 g of crude material. This latter was purified by means of crystallization in cyclohexane, m.p. 101°-104°, to give the desired compound.

Workup

  1. customwere reacted
  2. customThe crude reaction mixture
  3. extractionuntil neutrality, extraction with diethyl ether
  4. dry with materialdrying of the organic phase over Na2SO4 and evaporation
  5. customthere were isolated 0.4 g of crude material
  6. customThis latter was purified by means of crystallization in cyclohexane

Sources & evidence

ORD record
ord-010eb143092448c2b39ab92ac420777f
Source dataset
uspto-grants-1982_04
Patent number
US04324729

Reaction notes

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