Sulfuric Acid → 1-(2-Hydroxypropan-2-yl)-4-methylcyclohex-3-en-1-ol

HRID 1154063Notes

Reaction equation

HRID 1154063 reaction equation
[CH3:1][C:2]1([CH3:11])[C:4]2([CH2:9][CH2:8][C:7]([CH3:10])=[CH:6][CH2:5]2)[O:3]1.S(=O)(=O)(O)[OH:13]>>[OH:13][C:2]([C:4]1([OH:3])[CH2:9][CH2:8][C:7]([CH3:10])=[CH:6][CH2:5]1)([CH3:11])[CH3:1]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 1073031-Oxaspiro[2.5]oct-5-ene, 2,2,6-trimethyl-

Product 1

HCID 1796521-(2-Hydroxypropan-2-yl)-4-methylcyclohex-3-en-1-ol

Procedure

A mixture of 26.0 g of 2,2,6-trimethyl-1-oxaspiro(2.5)oct-5-ene and 250 ml of 1% sulfuric acid was stirred magnetically for 20 hours, then extracted with four 100 ml portions of methylene chloride. The combined methylene chloride extracts were washed, dried, concentrated and Claisen-distilled to give 22.4 g of the desired product, b.p. 78°-81° C. (0.15 mm).

Workup

  1. extractionextracted with four 100 ml portions of methylene chloride
  2. washThe combined methylene chloride extracts were washed
  3. customdried
  4. concentrationconcentrated
  5. distillationClaisen-distilled

Sources & evidence

ORD record
ord-318af6eb7e8448cb8c99715bffd6c806
Source dataset
uspto-grants-1984_12
Patent number
US04487945

Reaction notes

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